‘Sleeping with Other People’ Review: A Winning Raunchy Romcom

[This is a re-post of my Sleeping with Other People review from the 2015 Sundance Film Festival. The film is now playing in limited release.]

The romantic comedy genre is somewhat barren these days. It used to be that we’d regularly get genuinely good romantic comedies, but after too many lazy “nice girl makes slob boy clean up his act” films, the genre kind of died out. In its place came a slew of raunchy comedies geared towards adolescent men essentially shepherded by Judd Apatow. His brand (both as a director and producer) influenced a number of its own imitators, some good some bad, and the R-rated comedy is currently reigning supreme. But with Sleeping with Other People,writer/director Leslye Headland (Bachelorette)has found a way to combine the qualities that make those hard R-rated comedies so popular with the genuine emotion that permeated throughout the romcoms of the 80s and 90s, resulting in a hilarious, dirty, and ultimately sweet film.

Very much in the vein of When Harry Met Sally (in fact, Headland aptly describes the movie as “When Harry Met Sally with assholes”), Sleeping with Other People begins in 2002, as college students Jake (Jason Sudeikis) and Lainey (Alison Brie) meet when Lainey is chastised for banging on a door in the boy’s dormitories, the purpose of which was to convince her TA to sleep with her. Jake and Lainey bond over the course of the night as they speak in brutally honest terms about one another (Jake thinks the TA is the most boring person on the planet), and they end up losing their virginity to each other in what amounts to a one-night stand.

But they cross paths once more in present day New York City. Jake is attending a sex addict support group on orders from his girlfriend (he slept with her best friend), and he spots Lainey at the same meeting as well. She’s just come from confessing to her longtime boyfriend (Adam Brody in a hilariously scene-stealing performance) that she’s been having an affair. The object of Lainey’s infatuation is her OB-GYN Matthew (Adam Scott)—the same TA whom she was seeking out in college. They’ve been carrying on an intense affair, but after Lainey’s confession to her boyfriend, Matthew tells her that they shouldn’t see each other anymore as he’s just proposed to his girlfriend. They then proceed to have sex on his desk.

Image via IFC Films

As neither Jake nor Lainey are really having any luck forming sincere or healthy emotional attachments, they opt to go on a date to test the waters. The date goes well, but they decide they should remain friends and use a safe word whenever one becomes aroused by the other: “dick in a mousetrap”.

The relationship between Jake and Lainey develops deeply throughout the course of the film, as they confide in one another after bad/good hook-up experiences and take the opportunity to teach each other how to be better people, among other things. In a scene right out of When Harry Met Sally, Jake uses a bottle to teach Lainey how to…um…service herself. This is not really a movie you want to see with your parents.

Sleeping with Other People opens with Lainey’s meeting with her boyfriend in an intensely funny scene, but is then followed by a scene in which Lainey runs to the bathroom and has a bit of an emotional breakdown about just what happened. This clues the audience into the fact that, yes, this movie is going to be funny, but Headland is going to treat these characters as real human beings with emotional consequences.

Sudeikis is solidly cast as a bit of a smooth-talker and it’s easy to be coaxed by his charm even when he’s saying terrible things, while Brie imbues Lainey with an intelligence that shines through her recklessness. But at the heart of Jake and Lainey, they’re both essentially assholes. These are not the inherently nice Harry and Sally, they’re kind of dicks, and so the two are not immediately (or easily) likable. It takes a little while to get to a place where you’re rooting for them, but the story ultimately works thanks to the chemistry of Sudeikis and Brie. They may not be the best of people, but they certainly compliment each other.

Image via IFC Films

The supporting cast of the film is absolutely outstanding. It’s a series of standout comedic turns by folks like Amanda Peet, Andrea Savage, Natasha Lyonne, and the film’s MVP Jason Mantzoukas, who plays Jake’s friend and business partner. The comedy in the movie is really funny, but it’s also very raunchy. While it shouldn’t be a surprise given the film’s title, most of the scenes revolve around talking about sex in one form or another, and Sudeikis and Brie ping pong back and forth some filthy, though admittedly funny, dialogue.

Headland gives her cast some room to run free when it comes to ad-libbing, but enough scenes go on just a bit too long that you start to feel the film’s runtime. The riffing gets a little indulgent, but it does give way to plenty of gold from Mantzoukas. And the movie also boasts quite possibly the best Aaron Sorkin joke to date.

What’s admirable about Sleeping with Other People is that it treats its characters like grown-ups. While their asshole-ness somewhat diminishes the impact of the conclusion, Headland’s willingness to flesh out the characters emotionally as well as comedically is worth applauding, and there are genuine consequences for their actions. It’s also a wholly relatable premise that, again, speaks to the appeal of the romantic comedies of the 80s and 90s, and I’m happy to see some of that returning in this film. While the roughness of the characters may keep the film at a bit of a distance emotionally, Sleeping with Other People is a mostly satisfying romantic comedy with an edge that will leave you laughing very, very hard.

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